gay

Slang meaning "homosexual" (adj.) begins to appear in psychological writing late 1940s, evidently picked up from gay slang and not always easily distinguished from the older sense:

After discharge A.Z. lived for some time at home. He was not happy at the farm and went to a Western city where he associated with a homosexual crowd, being "gay," and wearing female clothes and makeup. He always wished others would make advances to him. ["Rorschach Research Exchange and Journal of Projective Techniques," 1947, p.240]

The association with (male) homosexuality likely got a boost from the term gay cat, used as far back as 1893 in American English for "young hobo," one who is new on the road, also one who sometimes does jobs.

"A Gay Cat," said he, "is a loafing laborer, who works maybe a week, gets his wages and vagabonds about hunting for another 'pick and shovel' job. Do you want to know where they got their monica (nickname) 'Gay Cat'? See, Kid, cats sneak about and scratch immediately after chumming with you and then get gay (fresh). That's why we call them 'Gay Cats'." [Leon Ray Livingston ("America's Most Celebrated Tramp"), "Life and Adventures of A-no. 1," 1910]

Quoting a tramp named Frenchy, who might not have known the origin. Gay cats were severely and cruelly abused by "real" tramps and bums, who considered them "an inferior order of beings who begs of and otherwise preys upon the bum -- as it were a jackal following up the king of beasts" [Prof. John J. McCook, "Tramps," in "The Public Treatment of Pauperism," 1893], but some accounts report certain older tramps would dominate a gay cat and employ him as a sort of slave. In "Sociology and Social Research" (1932-33) a paragraph on the "gay cat" phenomenon notes, "Homosexual practices are more common than rare in this group," and gey cat "homosexual boy" is attested in N. Erskine's 1933 dictionary of "Underworld & Prison Slang" (gey is a Scottish variant of gay).

The "Dictionary of American Slang" reports that gay (adj.) was used by homosexuals, among themselves, in this sense since at least 1920. Rawson ["Wicked Words"] notes a male prostitute using gay in reference to male homosexuals (but also to female prostitutes) in London's notorious Cleveland Street Scandal of 1889. Ayto ["20th Century Words"] calls attention to the ambiguous use of the word in the 1868 song "The Gay Young Clerk in the Dry Goods Store," by U.S. female impersonator Will S. Hays, but the word evidently was not popularly felt in this sense by wider society until the 1950s at the earliest.

"Gay" (or "gai") is now widely used in French, Dutch, Danish, Japanese, Swedish, and Catalan with the same sense as the English. It is coming into use in Germany and among the English-speaking upper classes of many cosmopolitan areas in other countries. [John Boswell, "Christianity, Social Tolerance, and Homosexuality," 1980]

Gay as a noun meaning "a (usually male) homosexual" is attested from 1971; in Middle English it meant "excellent person, noble lady, gallant knight," also "something gay or bright; an ornament or badge" (c.1400). As a slang word meaning "bad, inferior, undesirable," from 2000.